1957
DOI: 10.1021/jo01357a020
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By-products of the Willgerodt Reaction Applied to α- and γ- Picoline

Abstract: The solution was kept 1 hr. at -50°and warmed gradually over 2 hr. to -10°C. The liquid was washed with 300 ml. of 10% sodium sulfite, twice with water, and dried over anhydrous sodium sulfate. After evaporating chloroform, 151 g. (75%) of colorless 5,6-dichloro-l,3dioxepane boiling at 56°at 1 mm. was obtained.

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Cited by 24 publications
(3 citation statements)
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“…While several complexes featuring a thiol donor (i.e. R = H) are known, these compounds are also known to isomerize to form the corresponding benzothiazoline or benzothiazole, or to generate the corresponding disulfide . Introduction of a thioether substituent blocks this tautomerization, enabling the preparation of complexes of pmtpm ( L1 , Scheme 1) featuring manganese(I), iron(II), cobalt(II), nickel(II/III), and ruthenium(II) centers .…”
Section: Introductionmentioning
confidence: 99%
“…While several complexes featuring a thiol donor (i.e. R = H) are known, these compounds are also known to isomerize to form the corresponding benzothiazoline or benzothiazole, or to generate the corresponding disulfide . Introduction of a thioether substituent blocks this tautomerization, enabling the preparation of complexes of pmtpm ( L1 , Scheme 1) featuring manganese(I), iron(II), cobalt(II), nickel(II/III), and ruthenium(II) centers .…”
Section: Introductionmentioning
confidence: 99%
“…R = H) are known, these compounds are also known to isomerize to form the corresponding benzothiazoline or benzothiazole, or to generate the corresponding disulfide. [51][52][53][54][55] Introduction of a thioether substituent blocks this tautomerization, [56][57][58] enabling the preparation of complexes of pmtpm (1, Scheme 1) featuring manganese, 59 iron, 60 cobalt, 56 nickel, 61,62 and ruthenium. 63,64 Early reports emphasized the structural homology between these complexes and the related metalloenzymes (e.g.…”
Section: Introductionmentioning
confidence: 99%
“…The ligand N,N9-diphenylisonicotinamidine (L) was synthesized following literature techniques. 8 Two key features of this ligand are important for the formation of the dimer: it possesses a pyridyl group available for metal ion coordination and it has bulky phenyl rings that will encumber the axial site of the dimer and thus possible self-polymerisation by axial pyridine coordination. 9 The tetraamidinate complex (1) was synthesized by a melt reaction (Scheme 1).…”
mentioning
confidence: 99%